I would never have thought of pairing black loafers (or at least very dark loafers) with white trousers, but it looks very natural with that outfit.

That is a classic southern look, although I don't know if GW was going for that or even cares. Some of our members have received quite a thrashing for the look as a matter of fact. I think GW does it quite well.

I think the biggest problem with that for me is that I view the colors on top to be incongruous with the colors on bottom. The dark blue of the shirt and the brown/rust of the tie are very Fall, and the trousers are Summer all the way. I'm just not a big fan of the denim shirt with jacket/tie look either. Some will be more forgiving of this, but it's never a look I have liked.

I think the biggest problem with that for me is that I view the colors on top to be incongruous with the colors on bottom. The dark blue of the shirt and the brown/rust of the tie are very Fall, and the trousers are Summer all the way. I'm just not a big fan of the denim shirt with jacket/tie look either. Some will be more forgiving of this, but it's never a look I have liked.

The tie is a light brown knit so not sure if that helps haha, but I agree with the shirt. A washed out lighter shade would have been much better (if available).